Thiol-functionalized copolymeric polyesters by lipase-catalyzed esterification and transesterification of 1,12-dodecanedioic acid and its diethyl ester, respectively, with 1-thioglycerol

Biotechnology Letters

Volumn 32, Issue 10, 2010, Pages 1463-1471

  Fehling, Eberhard ^a   Bergander, Klaus ^b   Klein, Erika ^a   Weber, Nikolaus ^a   Vosmann, Klaus ^a  

^a FEDERAL RESEARCH INSTITUTE OF NUTRITION AND FOOD   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

1,12 Dodecanedioic acid; 1 Thioglycerol (3 mercaptopropane 1,2 diol); Esterification; Immobilized lipase B from Candida antarctica; Poly(1,12 dodecanedioic acid co 1 thioglycerol); Poly(diethyl 1,12 dodecanedioate co 1 thioglycerol)

Indexed keywords

1,12-DODECANEDIOIC ACID; 1-THIOGLYCEROL; DIETHYL ESTER; DRYING AGENT; FTIR; FUNCTIONALIZED; IMMOBILIZED LIPASE B FROM CANDIDA ANTARCTICA; LIPASE-CATALYZED; POLY(1,12-DODECANEDIOIC ACID-CO-1-THIOGLYCEROL); POLYCONDENSATES; POLYESTERIFICATION; POLYOXOESTERS; POLYTRANSESTERIFICATION; REACTION MIXTURE; SOLVENT FRACTIONATION; TRANSMETHYLATION;

CATALYSIS; DRYING; ESTERIFICATION; ESTERS; ISOMERS; YEAST;

ACIDS;

DICARBOXYLIC ACID; DODECANEDIOIC ACID; DRUG DERIVATIVE; GLYCEROL; IMMOBILIZED ENZYME; LIPASE B, CANDIDA ANTARCTICA; POLYESTER; THIOGLYCEROL; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA; CHEMISTRY; ENZYMOLOGY; ESTERIFICATION; GEL CHROMATOGRAPHY; INFRARED SPECTROSCOPY; ISOLATION AND PURIFICATION; MASS FRAGMENTOGRAPHY; METABOLISM; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CANDIDA; CHROMATOGRAPHY, GEL; DICARBOXYLIC ACIDS; ENZYMES, IMMOBILIZED; ESTERIFICATION; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; GLYCEROL; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR WEIGHT; POLYESTERS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

CANDIDA ANTARCTICA;

EID: 77956771648     PISSN: 01415492     EISSN: 15736776     Source Type: Journal    
DOI: 10.1007/s10529-010-0311-z     Document Type: Article

References (25)

1. Baldessari A, Iglesias LE, Gros EG (1993) Regioselective acylation of 3-mercaptopropane-1, 2-diol by lipase-catalyzed transesterification. J Chem Res S9: 382-383.
2. Fehling E, Klein E, Weber N, Demes C, Vosmann K (2007) Chemo-enzymatic preparation of copolymeric polythioesters containing branched-chain thioether groups. Appl Microbiol Biotechnol 74: 357-365.
3. Fehling E, Klein E, Vosmann K, Bergander K, Weber N (2008) Linear copolymeric poly(thia-alkanedioates) by lipase-catalyzed esterification and transesterification of 3, 3′-thiodipropionic acid and its dimethyl ester with α,ω-alkanediols. Biotechnol Bioeng 99: 1074-1084.
4. Gross RA, Kumar A, Kalra B (2001) Polymer synthesis by in vitro enzyme catalysis. Chem Rev 101: 2097-2124.
5. Iglesias LE, Baldessari A, Gros EG (1998) Lipase-catalyzed mono-O-acylation of dithiothreitol and dithioerythritol. Biotechnol Lett 20: 275-277.
6. Jendrossek D (2001) Microbial degradation of polyesters. Adv Biochem Eng/Biotechnol 71: 293-325.
7. Kazlauskas RJ, Bornscheuer UT (1998) Biotransformations with lipases. In: Rehm H-J, Reed G (eds) Biotechnology. Wiley-VCH, Weinheim, pp 37-191.
8. Kim YB, Lenz RW (2001) Polyesters from microorganisms. Adv Biochem Eng/Biotechnol 71: 51-79.
9. Kobayashi S, Uyama H (2001) In vitro biosynthesis of polyesters. Adv Biochem Eng/Biotechnol 71: 241-262.
10. Kúdelka I, Misro PK, Pospíšil J, Korbanka H, Riedel T, Pfahler G (1985) Antioxidants and stabilizers: Part IC-Hydroperoxide deactivation by aliphatic sulfides. A model study. Polymer Degr Stabil 12: 303-313.
11. Maignan J (2002) Polymers with thiol terminal function. US Patent 6395867, 28. 05. 2002.
12. Moad G, Rizzardo E, Thang SH (2007) Process for synthesizing thiol terminated polymers. WO Patent 2007/100719, 07. 09. 2007.
13. Nathan A (2007) Functionalized polymers for medical applications. US Patent 7253248, 07. 08. 2007.
14. Rehm BHA (2006) Genetics and biochemistry of polyhydroxyalkanoate granule self-assembly: the key role of polyester synthases. Biotechnol Lett 28: 207-213.
15. Shaglaeva NS, Amosova SV, Zavarzina GA, Sultangareev RG, Fedoseev AP, Kibort RG, Sergeeva EN (2005) Synthesis and antimicrobial activity of butadiene sulfide copolymers. Phar Chem J 39: 74-75.
16. Steinbüchel A (2005) Non-biodegradable biopolymers from renewable resources: perspectives and impacts. Curr Opinion Biotechnol 16: 607-613.
17. Steinbüchel A, Hein S (2001) Biochemical and molecular basis of microbial synthesis of polyhydroxyalkanoates in microorganisms. Adv Biochem Eng/Biotechnol 71: 81-123.
18. Takwa M, Hult K, Martinelle M (2008) Single-step, solvent-free enzymatic route to α,ω-functionalized polypentadecalactone macromonomers. Macromolecules 41: 5230-5236.
19. Tokiwa Y, Calabia BP (2004) Degradation of microbial polyesters. Biotechnol Lett 26: 1181-1189.
20. Uhrich KE (2003) Antibiotic polymers. WO Patent Appl 03/066053 A1, 14. 08. 2003.
21. Watanabe S, Ikeda R, Kitagawa H, Murata M, Masuda Y (2000) Synthesis of polymer microspheres with mercapto groups by polycondensation of α,ω-alkanedithiol and α,ω-dibromoalkane in the presence of a poly[styrene-N-(hydroxymethyl)acrylamide] latex. Macromol Chem Phys 201: 896-901.
22. Weber N, Klein E, Vosmann K (2006a) Dialkyl 3, 3′-thiodipropionate and 2, 2′-thiodiacetate antioxidants by lipase-catalyzed esterification and transesterification. J Agric Food Chem 54: 2957-2963.
23. Weber N, Bergander K, Fehling E, Klein E, Vosmann K, Mukherjee KD (2006b) Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of α,ω-alkanedithiols. Appl Microbiol Biotechnol 70: 290-297.
24. Wilczewska ZA, Destarac M, Zard S, Kalai C, Mignani G, Adam H (2002) Method for synthesis of polymers with thiol functions. WO Patent 2002/090424, 14. 11. 2002.
25. Yu Z, Miao G, Wu Q, Chen Y (1996) Synthesis of thiol- and carboxyl-terminated poly(p-phenylene sulfide) oligomers. Macromol Chem Phys 197: 4061-4068.